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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Thimble Islands holiday homes

Interior

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is HK$1,298
HK$3,165 total
includes taxes & fees
28 May - 29 May
Adorable Cottage, 5 min walk to water & town
1 bedroom, iron/ironing board, WiFi, bed sheets

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$924
HK$2,309 total
includes taxes & fees
3 Jun - 4 Jun
Once the old Schools house now a newly furnished Apartment
Smart TV, fireplace, books, offices

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
9.8 out of 10, Exceptional, (10 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is HK$2,272
HK$4,404 total
includes taxes & fees
28 May - 29 May
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Interior

Peaceful Private Stay in Shared Home Near Yale

Peaceful Private Stay in Shared Home Near Yale
West New Haven
10.0 out of 10, Exceptional, (1 review)
"This place was just perfect for us and our stay. The neighborhood was safe, and the property was easy to find. Bedroom was cozy, and the communication with the host was phenomenal. Thank you!"
United States
McKenna S.
The price is HK$1,269
HK$1,640 total
includes taxes & fees
28 May - 29 May
Peaceful Private Stay in Shared Home Near Yale
Interior

Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven

Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven
Foxon
The price is HK$1,058
HK$2,384 total
includes taxes & fees
3 Jun - 4 Jun
Quiet Comfort Meets Coastal Charm: A Perfect Family Retreat in East Haven
Interior

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (138 reviews)
"Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!"
United States
Hayley T.
The price is HK$2,586
HK$5,372 total
includes taxes & fees
28 May - 29 May
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Marina

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is HK$1,567
HK$2,773 total
includes taxes & fees
28 May - 29 May
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Dining

McAngel Haven: 5 mins from Yale

McAngel Haven: 5 mins from Yale
West Haven
9.6 out of 10, Exceptional, (21 reviews)
"Excellent location Clean and spacious Comfortable beds "
United States
Joseph T.
The price is HK$1,798
HK$4,129 total
includes taxes & fees
31 May - 1 Jun
McAngel Haven: 5 mins from Yale
Terrace/patio

The Jewel of The Cove - Historic Coastal Retreat

The Jewel of The Cove - Historic Coastal Retreat
East Shore
9.8 out of 10, Exceptional, (9 reviews)
"This was a great place to stay in New Haven, and a lot of care has gone into making it a welcoming house."
United States
Geoffrey H.
The price is HK$1,865
HK$4,245 total
includes taxes & fees
3 Jun - 4 Jun
The Jewel of The Cove - Historic Coastal Retreat
Interior

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches
East Shore
8.8 out of 10, Excellent, (3 reviews)
"Fantastic place, amazing hosts, 100% recommend! "
United States
Zach P.
The price is HK$2,532
HK$4,636 total
includes taxes & fees
9 Jun - 10 Jun
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches
2 bedrooms, desk, iron/ironing board, free WiFi

#37 - Luxury Collection

#37 - Luxury Collection
Stratford
8.4 out of 10, Very good, (5 reviews)
"We enjoyed the coziest getaway at this property. Newly renovated, clean and tucked away without being accessible to local attractions. "
United States
Sarah T.
The price is HK$1,207
HK$3,088 total
includes taxes & fees
28 May - 29 May
#37 - Luxury Collection
Terrace/patio

Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.2 out of 10, Wonderful, (90 reviews)
"This is a great location, walking distance to the green and other sites. It also worked well for our girls trip of 4 women."
United States
Liz H.
The price is HK$1,724
HK$4,208 total
includes taxes & fees
3 Jun - 4 Jun
Historic New England home ,Reunions Beach pass
TV, books

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
The price is HK$1,283
HK$3,791 total
includes taxes & fees
28 May - 29 May
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Private kitchen

Welcoming 4-bedroom house in charming Hamden

Welcoming 4-bedroom house in charming Hamden
Hamden
10.0 out of 10, Exceptional, (2 reviews)
"Host was kind and attentive. Location was convenient and the home was clean and spacious. "
United States
Renee H.
The price is HK$2,426
HK$4,146 total
includes taxes & fees
1 Jun - 2 Jun
Welcoming 4-bedroom house in charming Hamden
TV

Coastal Landing Stay

Coastal Landing Stay
East Shore
The price is HK$2,304
HK$4,309 total
includes taxes & fees
28 May - 29 May
Coastal Landing Stay
Interior

42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!
Milford
8.0 out of 10, Very good, (10 reviews)
"Beautiful cottage close to the beach. Very clean, easy check in process, would certainly recommend staying there again when in town "
United States
Crystal S.
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!
Smart TV, books

Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (11 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
The price is HK$4,506
HK$7,699 total
includes taxes & fees
28 May - 29 May
Clear LI Sound waterview, Wedding pics, Yale&Beach
Interior

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
9.8 out of 10, Exceptional, (27 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is HK$4,701
HK$7,596 total
includes taxes & fees
31 May - 1 Jun
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Terrace/patio

3-bedroom house just walking distance from Yale and Downtown

3-bedroom house just walking distance from Yale and Downtown
Dixwell
10.0 out of 10, Exceptional, (1 review)
"The house was extremely clean and convenient to downtown!"
United States
Lisa M.
The price is HK$1,959
HK$3,507 total
includes taxes & fees
28 May - 29 May
3-bedroom house just walking distance from Yale and Downtown
Smart TV, fireplace, video games

Steps to Beach • Hot Tub • Game Room • Water Views

Steps to Beach • Hot Tub • Game Room • Water Views
Branford
The price is HK$3,420
HK$6,449 total
includes taxes & fees
31 May - 1 Jun
Steps to Beach • Hot Tub • Game Room • Water Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Thimble Islands Hotel Reviews

Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven

10/10 Excellent
"Staff were professional."
Paul 1-night trip
Posted 1 hour ago
Hamden Hotel and Suites – Hamden New Haven

Find out more about Thimble Islands

Thimble Islands Vacation Homes information

Number of reviews
369
Accommodation
303 Vacation Homes
Lowest Price
HK$1,640
Highest Price
HK$7,699

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